Peekskill Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Peekskill vacation rentals

A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

1. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (43 reviews)
"We’ve actually stayed here twice so that should tell you we enjoy the space and the host is lovely."
United States
Heather M.
$341 nightly
The price is $390
Nov 10 - Nov 11
Total with taxes and fees
Contemporary Cozy Cottage
A house with a view of a bridge and mountains.

2. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (150 reviews)
"We had a great stay!!"
United States
Jasmine
$260 nightly
The price is $307
Dec 7 - Dec 8
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A spacious living area with a black leather sofa, a coffee table, a ceiling fan, and a blue cabinet.

3. Spacious 4-bedroom house in northern Westchester with sweeping views

Spacious 4-bedroom house in northern Westchester with sweeping views
Montrose
$523 nightly
The price is $598
Nov 8 - Nov 9
Total with taxes and fees
Spacious 4-bedroom house in northern Westchester with sweeping views
A modern kitchen with white cabinets, a wooden countertop, and a refrigerator.

4. Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.2 out of 10, Wonderful, (25 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
$283 nightly
The price is $286
Nov 9 - Nov 10
Total with taxes and fees
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
A house with a white front door, a small porch with a white railing, and a window with a green curtain.

5. Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.4 out of 10, Exceptional, (12 reviews)
"House was exactly as described. Would stay again."
United States
Beth M.
$256 nightly
The price is $281
Nov 8 - Nov 9
Total with taxes and fees
Fabulous 3bdrm Home w/parking!
A hallway with a wooden door, a black table with a sign, and large green plants.

6. 3BR Near West Point | Coffee Bar | Sleeps 6

3BR Near West Point | Coffee Bar | Sleeps 6
Highland Falls
10.0 out of 10, Exceptional, (3 reviews)
"Clean and convenient near West Point golf course"
United States
mario b.
$396 nightly
The price is $400
Nov 9 - Nov 10
Total with taxes and fees
3BR Near West Point | Coffee Bar | Sleeps 6
A modern kitchen with stainless steel appliances, wooden cabinets, and a contemporary light fixture.

7. Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Location was perfect for West Point visit. The space was clean and recently updated, the beds very comfortable, and perfect layout and spacious for 3-4 people. The host was welcoming and responsive."
United States
Maria L.
$217 nightly
The price is $239
Nov 8 - Nov 9
Total with taxes and fees
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
A dining table set with plates, cutlery, and glasses, with a bowl of fruit and a wine glass in the background.

8. Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
CROTON HDSN
9.8 out of 10, Exceptional, (95 reviews)
"The host, Maria, was excellent in staying in touch and personally met me upon check-in and checkout. The location is very convenient for walking around downtown or easily drive to nearby outings."
United States
Margaret S.
$309 nightly
The price is $354
Nov 12 - Nov 13
Total with taxes and fees
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
A modern living room with a stone fireplace, a leather sofa, a yellow armchair, a flat-screen TV, and a bookshelf.

9. 'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Croton-on-Hudson
10.0 out of 10, Exceptional, (9 reviews)
"We had an extended stay at Croton Quarters, it was great! The hosts truly are pet-friendly, the location is ideal, and the property comfortable for a longer term visit. "
United States
Mateo A.
$371 nightly
The price is $424
Nov 19 - Nov 20
Total with taxes and fees
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
A stone staircase leading to a house with a stone wall and a metal gate.

10. Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.

Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
Croton-on-Hudson
9.6 out of 10, Exceptional, (28 reviews)
"A lovely spot, very nice accommodations.Breakfast supples thoughtfully supplied as well as champagne to enjoy. "
United States
Eva C.
$343 nightly
The price is $392
Nov 9 - Nov 10
Total with taxes and fees
Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
A wooden deck with a table and chairs, overlooking a lake with cherry blossoms and autumn foliage.

11. Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms

Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
Lake Peekskill
10.0 out of 10, Exceptional, (1 review)
"We had an amazing stay at the lake house. The home is beautiful inside and out, and there is every amenity you could think of, from cooking and cleaning supplies to extra towels and blankets. The view of the lake is stunning and we enjoyed the peace and quiet of the little community. Linh is an excellent host and helped answer all of our questions. We will definitely be back!"
United States
Angel R.
$550 nightly
The price is $607
Nov 9 - Nov 10
Total with taxes and fees
Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
A bedroom with a bed, a ceiling fan, a window, and a painting on the wall.

12. Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.6 out of 10, Exceptional, (21 reviews)
"Great location! Easy checkin, checkout process. We would stay again"
United States
Morgan S.
$397 nightly
The price is $401
Nov 11 - Nov 12
Total with taxes and fees
Local Artist Inspired | Walk to WestPoint + King Bed
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

13. Hudson Valley/West Point Retreat w/ parking!

Hudson Valley/West Point Retreat w/ parking!
Highland Falls
$286 nightly
The price is $325
Nov 9 - Nov 10
Total with taxes and fees
Hudson Valley/West Point Retreat w/ parking!
A room with a wooden floor, a white door with a number, and a window with blinds.

14. Lovely 3BR Home with parking-Walk to WP Gate!

Lovely 3BR Home with parking-Walk to WP Gate!
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. "
United States
Briana T.
$274 nightly
The price is $311
Nov 9 - Nov 10
Total with taxes and fees
Lovely 3BR Home with parking-Walk to WP Gate!
A dining area with a table, chairs, a vase with flowers, a hanging light fixture, and wall decorations.

15. Mountain-View 2BR Steps from Thayer Gate

Mountain-View 2BR Steps from Thayer Gate
Highland Falls
$218 nightly
The price is $239
Nov 8 - Nov 9
Total with taxes and fees
Mountain-View 2BR Steps from Thayer Gate
A blue house with a white porch, a welcome sign, and a mailbox.

16. 3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed
Highland Falls
8.4 out of 10, Very good, (7 reviews)
"Space was excellent, the multiple bedrooms with the extra bathroom was great. Kitchen was stocked with utensils, bathrooms were clean, living space was comfortable and cozy."
United States
Christine T.
$394 nightly
The price is $448
Nov 10 - Nov 11
Total with taxes and fees
3BR West Point Retreat-3min to Back Gate+ King Bed
A wooden coffee table with two decorative planters in a living room.

17. Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!
Highland Falls
9.8 out of 10, Exceptional, (26 reviews)
"Clean, modern, functional, comfortable. Great stay"
United States
Jerell T.
$235 nightly
The price is $260
Nov 8 - Nov 9
Total with taxes and fees
Walk to WP Gate + Free Parking!
A living room with a wooden floor, a black sofa, a coffee table, and a ceiling fan.

18. Perfect 2BR with Free Parking! Walk to West Point!

Perfect 2BR with Free Parking! Walk to West Point!
Highland Falls
$233 nightly
The price is $257
Nov 9 - Nov 10
Total with taxes and fees
Perfect 2BR with Free Parking! Walk to West Point!
Living area

19. Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
8.4 out of 10, Very good, (5 reviews)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
$178 nightly
The price is $195
Dec 8 - Dec 9
Total with taxes and fees
Cozy 1-bedroom retreat minutes from West Point!
A deck with Adirondack chairs, a fire pit, and a grill.

20. 3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point

3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point
Cornwall
10.0 out of 10, Exceptional, (16 reviews)
"Everything you could ask for!!"
United States
Elisabeth
$357 nightly
The price is $422
Nov 9 - Nov 10
Total with taxes and fees
3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Find vacation rentals that suit your style

cabin image
Cabins
Cabins
Apartment image
Apartments
Apartments

Top Peekskill Hotel Reviews

A large, two-story white house with a wrap-around porch and a small front garden.
The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
Chester

10/10 Excellent

Lovely period home. Owners were friendly, courteous and informative. Breakfast was delicious. Overall stay was very enjoyable and would stay again.
United States
Cindy
Reviewed November 26, 2019
The Dominion House Bed & Breakfast

Find out more about Peekskill

Everything you need to know about Peekskill vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Peekskill vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Peekskill vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Peekskill vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Peekskill. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Peekskill in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $194 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Peekskill rentals

At Expedia, we put the best Peekskill vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Peekskill rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Peekskill vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Peekskill. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find a vacation rental in Peekskill?

Yes, there are vacation rentals in Peekskill close to Paramount Hudson Valley Theater, or you can go with a more remote option if you're looking for extra privacy while you relax. Nature enthusiasts will enjoy the riverfront and mountain landscape in Peekskill. While you're here, grab a bite or have a drink at the restaurants.

What are some of the best vacation rentals that Peekskill has to offer?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This vacation home rental near Peekskill offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with an oven, a microwave, and kitchenware, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Peekskill?

With 3 Expedia vacation rentals, you're sure to find just the right place for your Peekskill stay.

What’s there to see and do in Peekskill?

Enjoy the outdoors at Blue Mountain Reservation and Charles Point Pier Park, or simply take in cultural attractions like Paramount Hudson Valley Theater and Peekskill Museum. Other places in town to visit include Hudson Valley Center for Contemporary Art and Dramatic Hall.

What’s a vacation rental in Peekskill like?

Vacation rentals are privately owned properties you can book for a long or short time in Peekskill. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll feel right at home. If you're concerned about a clean environment, a vacation rental can provide a sense of seclusion away from public hotel elevators and busy front desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for family trips or small group gatherings.

Explore a world of travel with Expedia